Another idea I think would be fun, would be to do a sacvanger hunt, where the clues are the picture of where the next clue is. Like, start with a picture of Portlandia. Some where beneath her, I would have a picture of the man at Pioneer Court House Square. At the man I would have a picture the fountain by the Saturday Market, and so forth.
I think it would be fun, anyway. And that's all that counts, right?